Geraniol
Relevant Data
Food Additives Approved in the United States:
Food Additives Approved by WHO:
General Information
| Chemical name | Geraniol |
| CAS number | 106-24-1 |
| COE number | 60 |
| JECFA number | 1223 |
| Flavouring type | substances |
| FL No. | 02.012 |
| Mixture | No |
| Purity of the named substance at least 95% unless otherwise specified |
From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 637566 |
| IUPAC Name | (2E)-3,7-dimethylocta-2,6-dien-1-ol |
| InChI | InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+ |
| InChI Key | GLZPCOQZEFWAFX-JXMROGBWSA-N |
| Canonical SMILES | CC(=CCCC(=CCO)C)C |
| Molecular Formula | C10H18O |
| Wikipedia | geraniol |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 154.253 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 4 |
| Complexity | 150.0 |
| CACTVS Substructure Key Fingerprint | A A A D c e B w I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A D A C g g A I C A A A A A g C A A i B C A A A A A A A g A A A A C A A A A A g A F A I A A Q A A E A A A g A A I E A I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 20.2 |
| Monoisotopic Mass | 154.136 |
| Exact Mass | 154.136 |
| XLogP3 | None |
| XLogP3-AA | 2.9 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9375 |
| Human Intestinal Absorption | HIA+ | 0.9846 |
| Caco-2 Permeability | Caco2+ | 0.6445 |
| P-glycoprotein Substrate | Non-substrate | 0.5851 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8865 |
| Non-inhibitor | 0.5696 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8179 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5576 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7910 |
| CYP450 2D6 Substrate | Non-substrate | 0.8278 |
| CYP450 3A4 Substrate | Non-substrate | 0.5270 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9230 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9088 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7650 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7838 |
| Non-inhibitor | 0.8377 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.5055 |
| Fish Toxicity | High FHMT | 0.9236 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9864 |
| Honey Bee Toxicity | High HBT | 0.8229 |
| Biodegradation | Ready biodegradable | 0.8931 |
| Acute Oral Toxicity | III | 0.8552 |
| Carcinogenicity (Three-class) | Non-required | 0.6507 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.4720 | LogS |
| Caco-2 Permeability | 1.2481 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.6146 | LD50, mol/kg |
| Fish Toxicity | 0.6732 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0249 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | |
|---|---|
| Mechanism of Toxicity | |
| Metabolism | |
| Toxicity Values | |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | |
| Health Effects | |
| Treatment | |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Monoterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Acyclic monoterpenoids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Acyclic monoterpenoid - Fatty alcohol - Fatty acyl - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. |
From ClassyFire
Targets
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. Involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL. Can be activated by endogenous compounds, including 12-hydroperoxytetraenoic acid and bradykinin. Acts as ionotropic endocannabinoid receptor with central neuromodulatory effects. Triggers a form of long-term depression (TRPV1-LTD) mediated by the endocannabinoid anandamine in the hippocampus and nucleus accumbens by affecting AMPA receptors endocytosis (By similarity). Activation by vanilloids, like capsaicin, and temperatures higher than 42 degrees Celsius, exhibits a time- and Ca(2+)-dependent outward rectification, followed by a long-lasting refractory state. Mild extracellular acidic pH (6.5) potentiates channel activation by noxious heat and vanilloids, whereas acidic conditions (pH <6) directly activate the channel.
- Gene Name:
- TRPV1
- Uniprot ID:
- Q8NER1
- Molecular Weight:
- 94955.33 Da
References
- Ohkawara S, Tanaka-Kagawa T, Furukawa Y, Nishimura T, Jinno H: Activation of the human transient receptor potential vanilloid subtype 1 by essential oils. Biol Pharm Bull. 2010;33(8):1434-7. [20686244 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR: Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. [12495555 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR: Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. [12495555 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5 (By similarity). Specifically binds 9-cis retinoic acid (9C-RA).
- Gene Name:
- RXRB
- Uniprot ID:
- P28702
- Molecular Weight:
- 56921.38 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
From T3DB